On the Mechanism of Alkaline Hydrolysis of Methylthiopurines

Uri Reichman, Felix Bergman*, Dov Lichtenberg, Zohar Neiman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Di- and trimethylthiopurines, which can form anions, are resistant to alkaline hydrolysis. After introduction of an N-methyl substituent, these compounds are incapable of forming anions and become susceptible to attack by hydroxyl ion. The course of these reactions can be predicted satisfactorily by Fukui's superdelocalizabilities for nucleophilic attack; the same order of reactivities is derived for analogous methylthio- and chloropurines, in accordance with the limited experimental observations.

Original languageEnglish
Pages (from-to)2066-2073
Number of pages8
JournalJournal of Organic Chemistry
Issue number11
StatePublished - 1 Jun 1973
Externally publishedYes


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